It's the third day of the teachers' strike in Chicago. For the first time in 25 years, teachers are on the picket line and 350,000 students are out of class. The strike poses a unique challenge for Chicago's Mayor Rahm Emanuel. That's because he's also one of President Obama's top fund-raisers and surrogates.

From Chicago, NPR's Sonari Glinton reports.

SONARI GLINTON, BYLINE: Like most strikes, there are a whole bunch of chants. Here's the most interesting one for this story.

GLINTON: Mayor Rahm Emanuel is one of the focal points of the anger of Chicago teachers. That's in part because unlike in many other cities, Chicago's mayor has direct control of the school board.

Can you tell me what your sign says?

STEPHEN ROGERS: Emanuel sabotages Obama's election.

GLINTON: Stephen Rogers is a teacher at a Chicago public elementary school.

Why are so many people here frustrated with the mayor?

ROGERS: Because a lot of contracts are being pulled. It's not just teachers' contracts; firefighters, police officers, plumbers, taxi drivers. We all want a fair contract, and he's been pulling contracts and trying to cut stuff out of it.

GLINTON: When Emanuel arrived at city hall, he faced an array of problems: a city budget in deficit, a high murder rate, a culture of corruption in Chicago and a history of under-performing schools.

DICK SIMPSON: He's been able to get through some challenging situations, but this is the first crisis.

GLINTON: Dick Simpson is a former Chicago alderman who now teaches political science at the University of Illinois at Chicago. He says the mayor's now legendary personality is not exactly helping him in this crisis.

SIMPSON: Well, we expect our mayors to be tough. And we expect them to be strong. Abrasive isn't necessarily a good thing. He's managed to create an enemy that he didn't have when he came in office.

GLINTON: Here's an example of the mayor talking about some of the labor problems with teachers.

MAYOR RAHM EMANUEL: Teachers got two types of pay raises. And people in public life got labor peace. Can anybody explain to me what the children got?

GLINTON: The mayor decided to explain for himself.

EMANUEL: Our child got the shaft.

GLINTON: That was from a year ago. This is from yesterday.

EMANUEL: This was a strike of choice, and it's the wrong choice for the children. Really, it was a choice. We're down to two issues, having done five months of negotiations.

GLINTON: The two big issues that remain are job security and just how much weight to give a new evaluation system for teachers. David Stebenne is a labor historian at the Ohio State University. Stebenne says teachers' unions are particularly key for Democrats, especially because they turn out both volunteers and money.

DAVID STEBENNE: So the challenge for Democrats, if they're going to sort of be an effective mayor in a time of tight public budgets, is to restrict how much is paid to teachers and other public employees without alienating them completely.

GLINTON: Stebenne agrees with Dick Simpson that Emanuel's predecessors would likely have been more conciliatory. Mayor Richard M. Daley survived more than two decades without a teachers strike.

STEBENNE: Given the enormity of the problem facing the public school systems in places like Chicago and the other big cities that not being more adversarial or tough won't produce the desired result. And so that's why Emanuel is doing what he's doing, but it's not clear that it can be successful.

GLINTON: David Stebenne says Rahm Emanuel has a special problem that other big city mayors don't have. He was chief of staff for President Obama and is now mayor of the president's hometown. Stebenne says while fighting the teachers' union may not affect the election in Illinois, it could have other implications.

STEBENNE: If you make enemies in other states among teachers' unions, that's a more serious problem.

GLINTON: Both professors are quick to say that being mayor of any major city is a hard job. And maybe that's why so few of them move on to higher office. Sonari Glinton, NPR News, Chicago. Transcript provided by NPR, Copyright NPR.